HCID 91041030, compound → HCID 68644081, compound

HRID 1159190Notes

Reaction equation

HRID 1159190 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH:10]([N:15]=[N+]=[N-])[CH2:11][N:12]=[N+]=[N-])=[CH:4][CH:3]=1>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH:10]([NH2:15])[CH2:11][NH2:12])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 91041030HCID 91041030, compound

Product 1

HCID 68644081HCID 68644081, compoundYield 27.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of rac-1-chloro-4-(2,3-diazido-propoxy)-benzene (0.89 g, 3.5 mmol) in methanol (5 ml) was added palladium on charcoal (50 mg) and the mixture was hydrogenated at atmospheric pressure for 1 hour. The catalyst was removed by filtration over celite and the filtrate was evaporated. The residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate) to yield a light yellow liquid (0.19 g, 27%); MS (ISP): 201.3 ((M+H)+).

Workup

  1. customThe catalyst was removed by filtration over celite
  2. customthe filtrate was evaporated
  3. customThe residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate)

Sources & evidence

ORD record
ord-c05179f8fa254d43afea362d52c9580a
Source dataset
uspto-grants-2010_10
Patent number
US07812047B2

Reaction notes

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